Chiral sulfide and selenide catalysts for asymmetric halocyclizations and related reactions

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(16), P. 3263 - 3275

Published: Jan. 1, 2023

Recent advances in chiral sulfide-catalyzed asymmetric halocyclizations are summarized.

Language: Английский

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Cyclopropenium Sulfide as Lewis Base Catalyst for Chemoselective and Regioselective Electrophilic Selenylation of Phenols

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(12), P. 9198 - 9206

Published: June 1, 2024

Soft Lewis basic sulfides are frequently employed as catalysts in the electrophilic functionalization of unsaturated compounds because reactions can be operated under mild conditions. Among these reactions, selenylation less reported, partly due to lack sufficiently strong base catalysts. Herein, we report use cyclopropenium and soft for phenols. The catalytic protocol was also found useful late-stage modification tyrosine peptides. Mechanistic studies indicate that catalyst activate amide-type reagents by effective site isolation counteranion via nonclassical hydrogen bonds.

Language: Английский

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Differentiating the Allyl and Propargyl Groups on α‐Quaternary Carboxylic Acids via Chiral Bifunctional Sulfide‐Catalyzed Kinetic Resolution

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1496 - 1504

Published: April 15, 2023

Abstract Catalytic kinetic resolution of racemic organic compounds is a reliable method to enantioselectively prepare important chiral molecules. Substrates for the resolution, however, generally required significantly different substituents at center. molecules possessing two similar center has remained formidable challenge. In this context, we became interested in catalytic bearing both allyl and propargyl groups, which are but useful substituents, Herein, report α‐allyl‐α‐propargyl carboxylic acids an all‐carbon quaternary stereocenter via bifunctional sulfide‐catalyzed bromolactonization. The synthetic utility resultant optically active obtained was also demonstrated. magnified image

Language: Английский

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Chiral Organocatalysts in Enantioselective CO₂ Utilization Reactions

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(32)

Published: July 5, 2023

Abstract The development of efficient CO 2 utilization reactions has gained a significant amount attention in recent years. Although transformations to produce basic chemicals have been extensively investigated, the catalytic enantioselective for preparation fine remains limited at this stage. Several excellent methods using chiral metal complex catalysts reported. Many researchers also focused on developing organocatalyzed approaches utilization, and several examples appeared Herein, advances organocatalysts are reviewed provide forecast research.

Language: Английский

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Catalytic asymmetric CO₂ utilization reaction for the enantioselective synthesis of chiral 2-oxazolidinones

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(19), P. 4002 - 4006

Published: Jan. 1, 2023

Catalytic asymmetric bromocyclizations of in situ generated carbamic acids from CO2 and allylamines were achieved via the use a BINOL-derived chiral bifunctional selenide catalyst bearing hydroxy group. Chiral 2-oxazolidinone products as important pharmaceutical building blocks obtained with good enantioselectivities by present catalytic utilization reactions.

Language: Английский

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Chiral bifunctional sulfide-catalyzed enantioselective bromolactonizations of α- and β-substituted 5-hexenoic acids

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 1794 - 1799

Published: July 30, 2024

Enantioselective halolactonizations of sterically less hindered alkenoic acid substrates without substituents on the carbon–carbon double bond have remained a formidable challenge. To address this limitation, we report herein asymmetric bromolactonization 5-hexenoic derivatives catalyzed by BINOL-derived chiral bifunctional sulfide.

Language: Английский

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Chiral Bifunctional Sulfide-Catalyzed Enantioselective Synthesis of α-Substituted γ-Lactones Bearing a γ-Quaternary Stereocenter

Synlett, Journal Year: 2023, Volume and Issue: 35(04), P. 479 - 483

Published: Aug. 29, 2023

Abstract Catalytic highly enantioselective syntheses of α-spiro-γ-lactones and α-substituted γ-lactones bearing a γ-quaternary stereocenter have been achieved through chiral bifunctional sulfide-catalyzed asymmetric bromolactonizations. The synthetic utility the optically active γ-lactone products was demonstrated by transformations into functionalized epoxides possessing quaternary stereocenter.

Language: Английский

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Organocatalyzed Kinetic Resolution of Racemic Carboxylic Acids

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(1)

Published: Nov. 1, 2023

Abstract The kinetic resolution of racemic compounds is a reliable method to prepare important chiral molecules in highly optically enriched forms. Although methods for the catalytic alcohols, amines, and epoxides have been extensively investigated, carboxylic acids has remained under‐developed despite importance acids. Excellent approaches via esterification using organocatalysts reported by several research groups. Furthermore, organocatalyzed lactonization alkenyl alkynyl also adapted achieve resolution. Herein, typically used produce are reviewed elucidate current status this research.

Language: Английский

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Copper(I)‐Catalyzed Interrupted Click Reaction: Synthesis of 1,4,5‐Trisubstituted 5‐Chloro‐1,2,3‐Triazoles

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(42)

Published: Aug. 25, 2023

Abstract 5‐Halo‐1,2,3‐triazoles are important scaffolds in organic chemistry, but current click reactions cannot produce 1,4,5‐trisubstituted 5‐chloro‐1,2,3‐triazoles a simple way. Herein, we disclosed Cu(I)‐catalyzed interrupted reaction, using N ‐chlorophthalimide as an electrophilic chlorine source, enabling the facile synthesis of one step from readily available terminal alkynes and azides. Complete control regioselectivities with broad substrate scope was accomplished by this approach. Furthermore, novel epoxidation developed 5‐chloro‐triazole substrate, which could be further applied various transformations.

Language: Английский

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